Chemistry234
Chapter18ProblemSet
1. WritetheIUPACnameforeachether-containingcompoundshownbelow.Whereappropriate,also
includethecommonname.
O
O
Cl
O
Br
O
O
O
HO
2. Predictthemajororganicproductfromeachreactionbelow.
OH
1) NaH
2)
OH
Br
1) NaNH 2
2) Ph
Br
1) NaNH 2
OH
2)
Br
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Chem.234–Chapter18ProblemSet
3. DeterminetwodifferentroutestomakeeachetherbelowusingtheWilliamsonethersynthesis.
Indicatewhichroute(ifany)wouldbepreferred.
O
O
O
4. Drawacompleteelectronpushingmechanismforthereactionshownbelow.
OH
Cl
NaH
O
+ H 2 + NaCl
5. Predicttheproductforeachepoxidepreparationshownbelow.
mCPBA
mCPBA
Br
NaH
OH
OH
NaH
Br
OH
Br
NaNH 2
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Chem.234–Chapter18ProblemSet
6. Providethereagentsnecessarytocarryoutthefollowingtransformations.
Br
O
Br
O
7. Predicttheproductforeachofthereactionsshownbelow.
1) PhLi
O
2) H 2O
O
1) NaSH
2) H 2O
O
Ph
1) NaCN
2) H 2O
H
O
HBr
O
H 2SO 4
EtOH
H
H 2SO 4
O
H
O
CH 3OH
HCl
8. Providethenecessaryreagentstopreparethesyndiolandtheantidiolshownbelow.
OH
OH
+ en
HO
OH
+ en
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Chem.234–Chapter18ProblemSet
ChallengeProblems
9. Proposeanelectronpushingmechanismforthereactionshownbelow.
O
Et
Et
H 2SO 4
OH
O
10. Drawacompleteelectronpushingmechanismforthereactionshownbelow.
OH
O
HI
(excess)
I
I
+ H 2O
11. Providereasonablesyntheticroutestopreparethefollowingfrom2-methylbutane.
a. 1-methoxy-2-methyl-2-butanol
b. 1-methoxy-2-methylbutane
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